Synthesis of naturally occurring (+)-osmundalactone and 4-epi-(+)-osmundalactone from triacetyl-O-D-glucal

: Kotammagari TK, Gonnade RG, Bhattacharya AK

Publisher: PERGAMON-ELSEVIER SCIENCE LTD

: 2015

Tetrahedron Letters

: TETRAHEDRON LETTERS

: TETRAHEDRON LETT

: 56

: 21

: 2783

: 2786

: 4

: 0040-4039

DOI: https://doi.org/10.1016/j.tetlet.2015.04.038

An efficient total synthesis of (+)-osmundalactone 1 has been achieved starting from readily available triacetyl-O-D-glucal 6 employing Ferrier rearrangement and Jones oxidation as key steps. Also, synthesis of 4-epi-(+)-osmundalactone 2 was accomplished from the common key intermediate 9. The absolute stereochemistry of (+)-osmundalactone 1 and a precursor of 4-epi-(+)-osmundalactone 2 have been established by single crystal X-ray analysis. The overall yield of compound 1 and 2 from triacetyl-O-D-glucal 6 is 13% and 8%, respectively. (C) 2015 Elsevier Ltd. All rights reserved.